Big Water Fish Market. Photo by Thomas Bender

Staycationing on Siesta Key

My friend Amy and I refer to driving to Siesta Key as going “on vacation.” There is something that happens when we cross the bridge, Sarasota Bay behind us, and slip into a world of manicured mansions, pastel shop signs, and sweet, slushy frozen drinks. The omnipresent scent of sunscreen on skin takes me back in time to my own childhood beach vacations in California.

But, we rarely go to Siesta, whining, as year round residents of this tropical paradise do, about traffic and tourists.

However, as a frequent tourist in other people’s countries and cities, I know that just because something is touristy, it doesn’t automatically mean it is terrible. So, with a long weekend in front of me, I texted Amy: “Want to go ‘on vacation’?”

Day One:

9:45 a.m. Sarasota County Area Transit bus stop at Southgate Mall; 941-861-1234;

To keep my vacation as stress-free as possible, I left my car at home and took the SCAT Bus Route #10, which runs from the Southgate Mall through Siesta Key village and down the length of the island to Turtle Beach. I beat Amy, who drove, and our other friend Allie, who noted, “These ‘no parking’ signs are very aggressive.”

LeLu Coffee Lounge. Photo by Thomas Bender

10:15 a.m. Lelu Coffee, 5251 Ocean Blvd., Siesta Key; 941-346-5358;

I had met Lelu’s owner, Jennifer Suber Smith, through the Sarasota Whiskey Society, and knew her Hawaiian-style coffee shop also served craft cocktails, so I was excited to check it out. I ordered a Lelu Breakfast Samich ($8.25) and a Cafe Cubano ($2.50), and relaxed on the back patio, in the shade, next to an over-sized tiki mask, a collection of longboards, and tropical foliage. Vacation mode: activated.

Noon: Gidget’s Coastal Provisions, 5242 Ocean Blvd., Siesta Key; 941-343-7646;

It isn’t a real vacation without a souvenir, and Gidget’s aquamarine window displays were a soothing contrast to some of the more garish, day-glow ones across the street. Inside, among the collection of eclectic gifts, we each found the perfect things: a necklace with a Florida-shaped charm for me, and a small wood sign that said, “I Drink Wine and Rescue Dogs” for Amy.

1 p.m. Siesta Key Tropical Wines, 5138 Ocean Blvd., Siesta Key; 941-552-9105;

The hour or so Amy and I spent talking and wine tasting with Therese Rooney, who owns Siesta Key Tropical Wines with her mom, Maureen, yielded the greatest surprise of the trip: that some wines made in Florida (grapes are usually grown elsewhere) are actually good! Simply Key Lime ($20) made with sauvignon blanc grapes will make the perfect base for a white sangria. The shop stocks a small selection of wines from around the world, many of which are also available for tasting.

Meaney's Mini Donuts & Coffee House. Photo by Thomas Bender

Meaney’s Mini Donuts & Coffee House. Photo by Thomas Bender

3 p.m. Meaney’s Mini-Donuts, 205 Canal Road, Siesta Key

After wine-tasting, we needed a snack, so we crossed the street for Meaney’s Mini-Donuts. We shared a dozen donuts ($3.75) that, while tiny, are slightly bigger than your typical doughnut holes. The cinnamon-sugar ones taste like “upscale funnel cake” while the powdered sugar ones reminded us of the beignets from Cafe Du Monde in New Orleans; only smaller, denser, and less messy. “I could eat these while wearing black,” Allie said.

6:30 p.m. Cevichela, 5110 Ocean Blvd, Siesta Key; 941-349-0818;

Since we had only had doughnuts for lunch, we were all hungry and headed back to the Village to visit Cevichela for dinner. Darwin Santa Maria had previously owned one of our favorites, the now-closed Darwin’s on 4th in downtown Sarasota, so we were excited to visit his much smaller, more laid back Cevichela. Cevichela specializes in an array of innovative ceviche and customizable tacos, and reflects Santa Maria’s interest in craft beer by stocking a deep selection of local brews. Amy, who had been mourning the loss of Darwin’s chimichurri sauce, was elated to find it on the menu here.

8 p.m. Daiquiri Deck Siesta Key, 5250 Ocean Blvd., Siesta Key; 941-349-8697;

I opted to end my night at Daiquiri Deck where manager Eoin Farrell and his team make the high-volume restaurant and bar seem smaller- more like a a collection of local bars, each with their own personality. The best drink in the house is a PopCraft Daiquiri, which is a frozen drink that comes with a local, handmade frozen confection from my beloved PopCraft. Sadly, it was on hiatus until spring, so I chose the classic vacation libation, a rum runner.

The Tiny House Beach Resort. Photo by Thomas Bender

The Tiny House Beach Resort. Photo by Thomas Bender

Overnight: Tiny House Beach Resort, 6600 Ave. A, Sarasota; 941-474-3782; and

Located on the mainland side of Stickney Point bridge, Tiny House Beach Resort is a former mobile home and RV park that is being redeveloped by’s Jeremy Ricci into a tiny house village. When I visited, the first three of 12-plus homes were on site, with the others making their way from tiny home builders across the country. Layouts vary, but the most impressive had a master bedroom on the ground floor, a galley kitchen, and stairs leading up to two lofts, each with a queen or full size mattresses. Ricci is hopeful the resort will appeal to fans of the tiny house TV shows, as well as those who are “interested in the [tiny house] movement but might not want to live in one full-time,” he said. “This is an opportunity to try it out.”

Day Two:

9:00 a.m. Nutritious You, 6583 Midnight Pass Road, Siesta Key; 941-203-5203;

After my vacation-diet of fried dough and alcohol the day before, I was ready for something healthier and hopped on the SCAT bus #11. Nutritious You, hidden in the Southbridge strip mall behind the Taste of Germany Bakery, has been serving Siesta Key visitors raw, gluten-free, and vegan foods for several years. Walking in, owner-chef Marina Sommers offered me samples of the to-go items in the display case. After a breakfast smoothie ($8) and almond maca energy balls ($8.25), I bought her slightly spicy vegetable crackers ($7.50) and creamy cashew-based “jack cheese” ($3.75) for our mid-afternoon snacks.

Siesta Key Paddleboards. Courtesy photo

Siesta Key Paddleboards. Courtesy photo

10:30 a.m. Siesta Key Paddleboards, 941-301-8776;

My friends have been renting stand-up paddleboards from Dan Stein of the mobile Siesta Key Paddleboards for the past two years ($40/half-day; second board $30). He will drop off and pick up boards at several spots, but we chose the kayak launch on Turtle Beach, which eases paddlers into a gentle, placid lagoon where they can get their sea-legs and occasionally spot manatees. From there, we headed up the inlet and hugged the shore of the bay, threading through mangrove islands, until we reached the not-so-secret Secret Beach, which is only accessible by boat. Pulling up our boards onto a sandy spit, we then walked 10 feet to the gleaming white sands, azure water of the Gulf, and about 50 million less people than were on Siesta Key’s main beach the day before.

4 p.m Big Water Fish Market, 6641 Midnight Pass Road, Siesta Key; 941-554-8101;

What goes with sun and water sports better than a fresh seafood lunch? Big Water Fish Market is beloved by locals and visitors alike. It is worth fighting traffic to get their Steam Pot, similar to a shrimp boil, that overflows with crab legs, shrimp, potatoes, and corn. Specials change daily, but, when I visited, the lobster salad was light, slightly seasoned, and on a perfectly toasted bun.

5:30 p.m. The Orange Octopus, 1220 Old Stickney Point Road, Siesta Key; 941-346-0202;

There are so many ice-cream and gelato joints on Siesta Key that these could be the subject of their own article. The Orange Octopus, tucked back in the shopping center behind Captain Curt’s, is a locally owned, and has a cute parlor adjacent to the ice-cream counter that features old Florida photos. With a technically small (but actually very large) scoop of Kentucky Bourbon ice cream ($3.75) in hand, I walked back over the Stickney Point bridge to catch my bus home. Satiated, slightly sunburned, and totally relaxed, I reminded myself that 350,000 annual visitors can’t be wrong; how lucky we are to be able to live here and go “on vacation” anytime.


– By Jennifer Wells

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